A former Googler who is now CEO of her own startup asks all her employees to cold email their idol — here's why

Liz Wessel, CEO and cofounder of WayUp.
Courtesy of Liz Wessel
Liz Wessel says she has always been the type of person who has no shame in reaching out to someone, whether or not she knows the person.

Wessel is the CEO and cofounder of WayUp, a site used by hundreds of thousands of college students to find jobs at places like Microsoft, Uber, The New York Times, Disney, and Google — where Wessel previously worked.

Part of the reason she started WayUp with cofounder JJ Fliegelman was to combat nepotism, she says, "so it should make sense that I don't really care about whether I have connections to a person."

"In college, my best cold email was to Roelof Botha, one of the top venture capitalists in the world," she recalls. "He was a role model of mine, and I emailed him asking what he thought that I should do after I graduate in order to best position myself to one day start my own company: take a job offer at Google, or take a job offer at a venture-capital fund."

"He told me the former, and the rest was history," she says. "It's because of that first cold email that I have since always encouraged friends and colleagues to cold email people."

Wessel says she and Fliegelman started their company when they were just 24 and 25 years old. "We had a combined four years of full-time work experience, so there were often times that employees would ask us questions that we couldn't answer or would ask us for advice that we didn't want to get wrong," she says.

"So, we started encouraging the team to cold email people who would better know the answer. One of our company values is, 'Be a master at your craft, but know you're not the master.' So, I always encourage my team to cold email the actual masters in their respective fields."

Wessel and WayUp cofounder JJ Fliegelman.
Courtest of WayUp

During a trip to California in early 2015, Wessel says, she challenged her entire team to take advantage of the fact that they were surrounded by some of the greatest minds in tech.

"I told everyone to cold email one expert in Silicon Valley who they normally wouldn't have the guts to email and who they wouldn't be able to meet in New York City, where we're based," she says.

Wessel led by example. She emailed her biggest role model with a very personalized message, asking for 15 minutes of her time. "The email was sent at 2 a.m. on a Monday, and at 8 a.m. I got a response: She invited me to come to dinner at her house the next night," Wessel says. "This is a woman who probably gets more cold emails than 99% of the executives in the world, yet here she was, responding to me."

The rest of the team followed suit. And it worked.

Nikki Schlecker, the leader of WayUp's Brand team, for example, cold emailed Guy Kawasaki. The marketing exec, who was one of Apple's early employees, not only agreed to grab coffee with Schlecker — he also live-streamed the entire meeting.

The WayUp team (as of October).
Courtesy of WayUp

"I 'dare' my employees to do this because, in the past year and a half, I have learned more than I ever thought possible, and I want to make sure my employees are learning just as much," Wessel says. "As corny as it may sound, if you're not learning, you're not growing."

Another reason she does this: She strongly believes everyone should have at least one mentor — and cold emailing someone you admire is a great way to develop that type of relationship.

"Having a good mentor can keep you humble and motivated," she says. "Furthermore, it will help you learn more than reading a textbook or watching a how-to video. Nothing matters more to me than learning from great people, and when you're having a conversation with someone whose opinion you trust and value, and whose work you admire, it can help outline what success means to you, and the goals that you are working towards."

Wondering how to go about cold emailing your idol? Wessel shared a few tips:

Make the message personal. Do you have anything in common? Say what it is.

Keep the email short and sweet. If the person is busy, he or she won't want (or have time) to read an essay.

Say what you want to get out of the meeting, and let it be something small. "I'd like to pick your brain," or "I'd love to get your advice on something" are appropriate asks. Never, ever ask for a job in this first email!

Have an eye-catching subject line.

Make yourself sound interesting enough so that the person wants to meet with you.

Thank the person for his or her time and consideration.

"If you have someone in your field who inspires you to learn and understand how they got to where they are today," Wessel says, "it helps you create that mountaintop of your own."